EP1398355A1 - Zusammensetzung zur Färbung von keratinischen Fasern enthaltend einen monoazo monokationischen Farbstoff - Google Patents
Zusammensetzung zur Färbung von keratinischen Fasern enthaltend einen monoazo monokationischen Farbstoff Download PDFInfo
- Publication number
- EP1398355A1 EP1398355A1 EP03292224A EP03292224A EP1398355A1 EP 1398355 A1 EP1398355 A1 EP 1398355A1 EP 03292224 A EP03292224 A EP 03292224A EP 03292224 A EP03292224 A EP 03292224A EP 1398355 A1 EP1398355 A1 EP 1398355A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- amino
- ium
- pyrrolophényl
- pyridin
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 111
- 238000004043 dyeing Methods 0.000 title claims abstract description 27
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 14
- 239000000835 fiber Substances 0.000 claims abstract description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 239000007800 oxidant agent Substances 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 230000003647 oxidation Effects 0.000 claims abstract description 22
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 150000003568 thioethers Chemical class 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 11
- 150000001450 anions Chemical class 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 238000009967 direct dyeing Methods 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 5
- -1 hydroxy radicals Chemical class 0.000 claims description 127
- 239000000975 dye Substances 0.000 claims description 93
- 150000003254 radicals Chemical class 0.000 claims description 80
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 239000000982 direct dye Substances 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 102000011782 Keratins Human genes 0.000 claims description 24
- 108010076876 Keratins Proteins 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- 125000002091 cationic group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 150000002430 hydrocarbons Chemical group 0.000 claims description 13
- 230000001590 oxidative effect Effects 0.000 claims description 13
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract description 6
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 2
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- AMSDWLOANMAILF-UHFFFAOYSA-O 2-(1h-imidazol-3-ium-3-yl)ethanol Chemical compound OCC[NH+]1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-O 0.000 description 17
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 14
- 239000012429 reaction media Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000004040 coloring Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- ACVSHQGHCWUJFU-UHFFFAOYSA-N 2h-imidazole Chemical compound C1N=CC=N1 ACVSHQGHCWUJFU-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
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- 235000010755 mineral Nutrition 0.000 description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 4
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 3
- RNBYZDHZDDTSLN-UHFFFAOYSA-N 2-(1h-imidazol-3-ium-3-yl)ethanol;chloride Chemical compound [Cl-].OCCN1C=C[NH+]=C1 RNBYZDHZDDTSLN-UHFFFAOYSA-N 0.000 description 3
- FNUKLSVGSFFSLI-UHFFFAOYSA-N 2-(3-aminophenyl)ethanol Chemical compound NC1=CC=CC(CCO)=C1 FNUKLSVGSFFSLI-UHFFFAOYSA-N 0.000 description 3
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- 125000004663 dialkyl amino group Chemical group 0.000 description 3
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- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 2
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- 229920006318 anionic polymer Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SWXQKHHHCFXQJF-UHFFFAOYSA-N azane;hydrogen peroxide Chemical compound [NH4+].[O-]O SWXQKHHHCFXQJF-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- VYTBDSUNRJYVHL-UHFFFAOYSA-N beta-Hydrojuglone Natural products O=C1CCC(=O)C2=C1C=CC=C2O VYTBDSUNRJYVHL-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- DGQLVPJVXFOQEV-NGOCYOHBSA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-NGOCYOHBSA-N 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 229940114118 carminic acid Drugs 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- 150000001783 ceramides Chemical class 0.000 description 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 235000012754 curcumin Nutrition 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 229940109262 curcumin Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- CSFWPUWCSPOLJW-UHFFFAOYSA-N hydroxynaphthoquinone Natural products C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- CXORMDKZEUMQHX-UHFFFAOYSA-N kermesic acid Chemical compound O=C1C2=C(O)C(O)=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C CXORMDKZEUMQHX-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- BKEFUBHXUTWQED-UHFFFAOYSA-N n-(4-amino-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C(O)=C1 BKEFUBHXUTWQED-UHFFFAOYSA-N 0.000 description 1
- FGVWHENWNJKCEH-UHFFFAOYSA-N n-methyl-n-[(1-methylpyridin-1-ium-4-yl)methylideneamino]aniline Chemical compound C=1C=CC=CC=1N(C)N=CC1=CC=[N+](C)C=C1 FGVWHENWNJKCEH-UHFFFAOYSA-N 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- SPDFSSLYVRCMDZ-UHFFFAOYSA-N octane-2,5-dione Chemical compound CCCC(=O)CCC(C)=O SPDFSSLYVRCMDZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- WDGFFVCWBZVLCE-UHFFFAOYSA-N purpurogallin Chemical compound C1=CC=C(O)C(=O)C2=C1C=C(O)C(O)=C2O WDGFFVCWBZVLCE-UHFFFAOYSA-N 0.000 description 1
- FFNJDUZBKSGSIV-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,5-diamine Chemical compound C1=CC(N)=NC2=C(N)C=NN21 FFNJDUZBKSGSIV-UHFFFAOYSA-N 0.000 description 1
- PNFZIEOWPDFJBH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C=NN21 PNFZIEOWPDFJBH-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/12—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom
- C09B44/126—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom in a six-membered ring, e.g. pyrridinium, quinolinium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/16—1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium
Definitions
- the subject of the invention is a new composition for dyeing human keratin fibers and more particularly the hair, containing a particular monoocation monoazo dye, as well as the processes for dyeing fibers using such a composition.
- a subject of the invention is also the use of these dyes as direct dyes, and the new monoocation monoazo dyes.
- oxidation bases we also know that we can vary the nuances obtained with these oxidation bases by associating them with couplers or color modifiers, the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds such as as indole compounds.
- couplers or color modifiers the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds such as as indole compounds.
- couplers or color modifiers the variety of molecules involved in the oxidation bases and couplers allows obtaining a rich palette of colors.
- This oxidation dyeing process consists in applying to the keratin fibers, oxidation bases or a mixture of oxidation bases and couplers with an oxidizing agent, for example hydrogen peroxide, to leave on, then to rinse the fibers.
- the resulting colorings are permanent, powerful, and resistant to external agents, in particular to light, bad weather, washing, perspiration and
- the lightening of the fiber has the advantageous effect of generating a solid color in the case of gray hair, and in the case of naturally pigmented hair, of bringing out the color, that is to say making it more visible.
- direct dyeing It is also known to dye human keratin fibers by direct coloring.
- the method conventionally used in direct dyeing consists in applying direct dyes to the fibers which are colored and coloring molecules having an affinity for the fibers, allowing them to stand, then rinsing the fibers. It is known, for example, to use direct benzene, anthraquinone, nitropyridine dyes, azo, xanthene, acridine dye or triarylmethane dye.
- the resulting colorings are particularly chromatic colors which are however temporary or semi-permanent because the nature of the interactions which bind the direct dyes to the fiber, and their desorption from the surface and / or from the core of the fiber are responsible for their low dye power and poor resistance to washing or perspiration.
- These direct dyes are also generally sensitive to light due to the low resistance of the chromophore vis-à-vis photochemical attacks and lead over time to a fading of the coloring of the hair. In addition, their sensitivity to light is dependent on their uniform or aggregate distribution in the keratin fiber. It is known to use direct dyes in combination with oxidizing agents.
- direct dyes are generally sensitive to the action of oxidizing agents such as hydrogen peroxide, and reducing agents such as sodium bisulfite, which makes them generally difficult to use in lightening direct dye compositions based on hydrogen peroxide and based on an alkalizing agent or in oxidation dye compositions in association with precursors of oxidation dyes or couplers.
- oxidizing agents such as hydrogen peroxide
- reducing agents such as sodium bisulfite
- branched hydrocarbon chain means a chain can form one or more carbon rings with 3 to 6 links.
- unsaturated hydrocarbon chain a chain can include one or more several double bonds and / or one or more triple bonds, this chain hydrocarbon which can lead to aromatic groups.
- X- represents a cosmetically acceptable organic or inorganic anion, for example chosen from a halide such as chloride, bromide, fluoride, iodide; a hydroxide; a sulfate; a hydrogen sulfate; a (C 1 -C 6 ) alkyl sulphate such as for example a methyl sulphate or an ethyl sulphate; an acetate; a tartrate; an oxalate; a (C 1 -C 6 ) alkyl sulfonate such as methylsulfonate; an arylsulfonate substituted or unsubstituted by a C 1 -C 4 alkyl radical such as for example a 4-toluylsulfonate.
- a halide such as chloride, bromide, fluoride, iodide
- a hydroxide such as chloride, bromide, fluoride, io
- W 3 (formula I) represents a hydrogen atom or a C 1 -C 4 alkyl radical optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy radicals, amino, (di) C 1 -C 2 alkylamino.
- W 3 (formula I) represents a hydrogen atom or a methyl, ethyl, 2-hydroxyethyl radical, and even more particularly a hydrogen atom.
- W 5 (formula I) is chosen from pyrazolyl, pyrrolyl and imidazolyl rings, and more particularly still from pyrrolyl and imidazolyl rings.
- W 5 is a 5-membered nitrogen-heteroaromatic ring substituted by one or more C 1 -C 6 alkyl radicals optionally substituted by hydroxy, C 1 -C 4 alkoxy, amino, mono or C 1 -C 4 dialkylamino; a chlorine or fluorine atom; a C 1 -C 4 alkoxycarbonyl radical; a phenyl radical optionally substituted by a hydroxy, C 1 -C 2 alkoxy, amino, mono or C 1 -C 2 dialkylamino, a bromine or chlorine atom; a dialkylamino radical in C 1 -C 2 alkoxy, C 1 -C 2.
- W 5 is more particularly chosen from pyrrolyl, imidazolyl radicals which are optionally substituted with one to two methyl, ethyl, propyl, phenyl, 4-chlorophenyl, ethoxycarbonyl radicals.
- R 1 , R 2 , R 9 and R 12 preferably represent, identical or different, a C 1 -C 4 alkyl radical optionally substituted by one or more radicals chosen from hydroxy, C 1 -C alkoxy radicals 2 , amino, (di) C 1 -C 2 alkylamino.
- R 1 , R 2 , R 9 , R 12 represent, identical or different, a methyl, ethyl, propyl, 2-hydroxyethyl radical.
- R 5 , R 6 , R 7 and R 8 are preferably chosen, identical or different, from a hydrogen atom, a methyl, ethyl, isopropyl, methoxymethyl, hydroxymethyl, 1-carboxymethyl, 1-aminomethyl radical.
- R 5 , R 6 , R 7 and R 8 are chosen, identical or different, from a hydrogen atom, a methyl, hydroxymethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, methoxy radical. , 2-hydroxyethyloxy, and even more preferably from a hydrogen atom, a methyl radical, a methoxy radical.
- R 3 , R 4 , R 10 , R 11 , R 13 , R 14 and R 15 are preferably chosen from a hydrogen atom; a linear or branched C 1 -C 4 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, (poly) hydroxy C 2 -C 4 alkoxy, amino, (di ) C 1 -C 2 alkylamino; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, (poly) hydroxy C 2 -C 4 alkoxy, amino, (di) C 1 -C 2 alkylamino, or a halogen atom such as chlorine, fluorine or bromine; a sulfonylamino radical; a C 1 -C 2 alkoxy radical; a C 2 -C 4 (poly) hydroxyalkoxy
- R 3 , R 4 , R 10 , R 11 , R 13 , R 14 and R 15 represent, identical or different, a hydrogen atom, a C 1 -C 4 alkyl radical optionally substituted by one or more radicals chosen from hydroxy, amino and (di) C 1 -C 2 alkylamino radicals; a C 1 -C 2 alkoxy radical; an amino radical; a C 1 -C 2 (di) alkylamino radical; a C 2 -C 4 (poly) hydroxyalkylamino radical.
- R 3 , R 4 , R 10 , R 11 , R 13 , R 14 and R 15 represent, identical or different, a hydrogen atom, a methyl, phenyl, 2-hydroxymethyl radical, methoxy, ethoxy, 2-hydroxyethyloxy, amino, methylamino, dimethylamino, 2-hydroxyethylamino.
- Z 1 denotes NR 2 .
- Z 2 denotes CR 4 .
- Z 3 denotes CR 13 .
- Z 4 denotes CR 14 .
- Z 5 denotes CR 15 .
- the concentration of monoocation monoazo dye of formula (I) can vary from about 0.001 to 5% by weight relative to the total weight of the composition dye, and preferably about 0.05 to 2%.
- the dye composition in accordance with the invention may also contain direct dyes different from those of formula (I), these dyes can in particular be chosen from neutral, acid or cationic benzene nitro direct dyes, acid or cationic neutral azo direct dyes, quinone direct dyes and in particular neutral, acidic or cationic anthraquinonics, direct dyes azine, methine direct dyes, direct dyes tetraazapentamethines, triarylmethane direct dyes, direct dyes Indoamines and natural direct dyes.
- direct dyes different from those of formula (I) these dyes can in particular be chosen from neutral, acid or cationic benzene nitro direct dyes, acid or cationic neutral azo direct dyes, quinone direct dyes and in particular neutral, acidic or cationic anthraquinonics, direct dyes azine, methine direct dyes, direct dyes tetraazapentamethines, triarylmethane direct dyes,
- the additional direct dye (s) preferably represent from 0.001 to 20% by weight approximately of the total weight of the composition and even more preferably from 0.005 to 10% by weight approx.
- composition of the invention may also comprise an oxidizing agent.
- This agent oxidizing agent can be any oxidizing agent conventionally used for the discoloration of human keratin fibers.
- the oxidizing agent is preferably chosen among hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and enzymes among which may be mentioned peroxidases, oxidoreductases with 2 electrons such as uricases and 4-electron oxygenases such as laccases.
- peroxide hydrogen is particularly preferred.
- composition according to the invention when intended for a conventional oxidation dye, it further comprises an oxidation base.
- This oxidation base can be chosen among the oxidation bases conventionally used in oxidation dyeing, for example para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
- paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine , 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline , 2- ⁇ -hydroxyethyl para
- paraphenylenediamine paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 2-chloro paraphenylenediamine, 2- ⁇ -acetylaminoethyloxy paraphenylenediamine, and their addition salts with an acid are particularly preferred .
- the bis-phenylalkylenediamines there may be mentioned by way of example, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1,3-diamino propanol, N , N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N ' -bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis- (2,
- para-aminophenol there may be mentioned, by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
- ortho-aminophenols there may be mentioned by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid.
- heterocyclic bases that may be mentioned by way of example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
- pyridine derivatives mention may be made of the compounds described for example in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino 6-methoxy pyridine, 2- ( ⁇ -methoxyethyl) amino 3-amino 6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
- pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2,359,399; JP 88-169,571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765 such as 2,4,5,6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy 5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which may be mentioned pyrazolo - [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3
- composition according to the invention may also contain one or more couplers conventionally used for the conventional oxidation dyeing of human keratin fibers.
- couplers conventionally used for the conventional oxidation dyeing of human keratin fibers.
- couplers mention may in particular be made of metaphenylenediamines, meta-aminophenols, metadiphenols, naphthalene couplers and heterocyclic couplers.
- the coupler (s) are generally present in an amount between 0.001 and 10% by weight approximately of the total weight of the dye composition and more preferably from 0.005 to 6%.
- the oxidation base (s) are present in an amount preferably between 0.001 to 10% by weight approximately of the total weight of the dye composition, and more preferably from 0.005 to 6%.
- the addition salts with an acid which can be used in the framework of the dye compositions of the invention for oxidation bases and couplers are especially chosen from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
- the cosmetically acceptable medium for dyeing also called dye support, generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
- organic solvent mention may, for example, be made of lower C 1 -C 4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
- the solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
- the dye composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or mixtures thereof, mineral or organic thickening agents, and in particular associative anionic, cationic, nonionic and amphoteric polymeric thickeners, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.
- adjuvants above are generally present in an amount for each of them of between 0.01 and 20% by weight relative to the weight of the composition.
- the pH of the dye composition in accordance with the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers or even using conventional buffer systems.
- acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
- basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (VI) below: in which W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical; R 16, R 17, R 18 and R 19, identical or different, represent a hydrogen atom, an alkyl radical in C 1 -C 4 hydroxyalkyl or C 1 -C 4.
- the dye composition according to the invention can be in forms various, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing human keratin fibers, and in particular hair.
- the invention also relates to a direct dyeing process which comprises the application of a dye composition comprising a dye of formula (I) as defined above, on human keratin fibers. After a pause, the fibers are rinsed leaving colored fibers to appear.
- the application to the fibers of the dye composition comprising the monoazo dye monoocationic of formula (1) can be used in the presence of an oxidizing agent which causes the discoloration of the fiber (the dyeing process then constitutes a dyeing process direct lightening).
- This oxidizing agent can be added to the composition containing the dye of formula (I) at the time of use or directly on the fiber.
- the invention also relates to an oxidation dyeing process which comprises the application to human keratin fibers of a dye composition which comprises a dye of formula (I), at least one oxidation base and optionally at least a coupler, in the presence of an oxidizing agent.
- a dye composition which comprises a dye of formula (I), at least one oxidation base and optionally at least a coupler, in the presence of an oxidizing agent.
- the oxidation base, the coupler and the oxidizing agent are as defined above.
- the color can be revealed at acidic, neutral or alkaline pH and the oxidizing agent can be added to the composition of the invention just at the time of use or it can be used from an oxidizing composition containing it , applied to the fibers simultaneously or sequentially to the dye composition.
- the dye composition is mixed, preferably at the time of use, with a composition containing, in a cosmetically acceptable medium, at least one oxidizing agent, this agent oxidant being present in an amount sufficient to develop coloration.
- a composition containing, in a cosmetically acceptable medium, at least one oxidizing agent, this agent oxidant being present in an amount sufficient to develop coloration is then applied to the fibers. After a pause time of approximately 3 to 50 minutes, preferably approximately 5 to 30 minutes, the fibers are rinsed, washed with shampoo, rinsed again and then dried.
- the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
- the pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dye composition, the pH of the resulting composition applied to human keratin fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 11. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing human keratin fibers and as defined above.
- the composition which is finally applied to the fibers can be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing human keratin fibers, and in particular the hair.
- Another object of the invention is a device with several compartments or "kit” dye in which a first compartment contains the dye composition of the invention and a second compartment contains the oxidizing composition.
- These measures can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.
- the dyes of formula (I) can be obtained from methods of preparation known and described for example in documents DE-19 721619, or US-5 852,179.
- the dye according to the invention of the following formula was prepared: 2- (4-amino-N- (4- (N-pyrrolophenyl)) - phenylazo) -1,3-dimethyl-3H-imidazol-1-ium acetate.
- the dye according to the invention of the following formula was prepared: 2- (4-amino-N- (4- (N- (2,5-dimethyl) -pyrrolophenyl)) - phenylazo) -1,3-dimethyl-3H-imidazol-1-ium chloride.
- the dye according to the invention of the following formula was prepared: 2- (4-amino-N- (4- (N- (2-methyl-5-propyl) -pyrrolophenyl)) - phenylazo) -1,3-dimethyl-3H-imidazol-1-ium chloride.
- the dye according to the invention of the following formula was prepared: 2- (4-amino-N- (4- (N- (2-methyl-5-phenyl) -pyrrolophenyl)) - phenylazo) -1,3-dimethyl-3H-imidazol-1-ium chloride.
- the dye according to the invention of the following formula was prepared: 2- (4-amino-N- (4- (N- [2-methyl-3-carboxyethyl-5- (4-chlorophenyl) -pyrrolophenyl)] - phenylazo) -1,3-dimethyl-3H-imidazol chloride -1 -ium.
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0211186 | 2002-09-10 | ||
FR0211186A FR2844269B1 (fr) | 2002-09-10 | 2002-09-10 | Composition pour la teinture des fibres keratiniques humaines comprenant un colorant monoazoique monocationique |
Publications (1)
Publication Number | Publication Date |
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EP1398355A1 true EP1398355A1 (de) | 2004-03-17 |
Family
ID=31725967
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03292224A Withdrawn EP1398355A1 (de) | 2002-09-10 | 2003-09-10 | Zusammensetzung zur Färbung von keratinischen Fasern enthaltend einen monoazo monokationischen Farbstoff |
Country Status (2)
Country | Link |
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EP (1) | EP1398355A1 (de) |
FR (1) | FR2844269B1 (de) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE602004016467D1 (de) * | 2004-05-22 | 2008-10-23 | Kpss Kao Gmbh | Zusammensetzung zur Aufhellung und Färbung der Keratinfasern |
FR2878154B1 (fr) | 2004-11-25 | 2007-02-09 | Oreal | Composition aqueuse de coloration des fibres keratiniques comprenant un colorant et un copolymere blocs particulier |
US7396368B2 (en) | 2004-12-15 | 2008-07-08 | L'oreal S.A. | Symmetrical diazo compounds comprising 4-pyridinium groups and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device |
FR2879195B1 (fr) | 2004-12-15 | 2007-03-02 | Oreal | Composes diazoiques symetriques a groupements 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif |
FR2879192B1 (fr) | 2004-12-15 | 2007-02-02 | Oreal | Composes diazoiques dissymetriques a groupement 2-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif |
FR2879199B1 (fr) | 2004-12-15 | 2007-02-02 | Oreal | Composes diazoiques symetriques a groupements 2-imidazolium et bras de liaison cationique, compositions les comprenant, procede de coloration et dispositif |
FR2879200B1 (fr) | 2004-12-15 | 2007-02-02 | Oreal | Composes diazoiques symetriques a groupements 4-pyridium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif |
US7438728B2 (en) | 2004-12-15 | 2008-10-21 | L'oreal S.A. | Dissymmetrical diazo compounds comprising 2-pyridinium group and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device |
US7247713B2 (en) | 2004-12-15 | 2007-07-24 | L'oreal, S.A. | Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
FR2879196B1 (fr) | 2004-12-15 | 2007-03-02 | Oreal | Composes diaz0iques symetriques a groupements 2-imidazolium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif |
US7288639B2 (en) | 2004-12-15 | 2007-10-30 | L'oreal S.A. | Dyssymmetrical diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker, compositions comprising them, method of coloring, and device |
FR2879193B1 (fr) | 2004-12-15 | 2007-08-03 | Oreal | Composes diazoiques dissymetriques presentant au moins un motif 2-imidazolium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif |
FR2879190B1 (fr) | 2004-12-15 | 2007-03-02 | Oreal | Composes diazoiques dissymetriques presentant au moins un motif 4-pyridinium et bras de liaison cationique ou non, compositions les comprenant, procede de coloration et dispositif |
FR2882519B1 (fr) | 2005-02-28 | 2008-12-26 | Oreal | Coloration de matieres keratiniques notamment humaines par transfert thermique a sec d'un colorant direct azomethinique composition comprenant ledit colorant et son procede de preparation |
FR2882521B1 (fr) | 2005-02-28 | 2008-05-09 | Oreal | Coloration de matieres keratiniques notamment humaines par transfert thermique a sec d'un colorant direct, composition comprenant ledit colorant et son procede de preparation |
FR2882518B1 (fr) | 2005-02-28 | 2012-10-19 | Oreal | Coloration de matieres keratiniques notamment humaines par transfert thermique a sec d'un colorant direct anthraquinonique, composition comprenant ledit colorant et son procede de preparation |
FR2882560B1 (fr) | 2005-02-28 | 2007-05-18 | Oreal | Composition anhydre sous forme de film comprenant un polymere filmogene et un colorant d'oxydation, preparation et procede de coloration la mettant en oeuvre |
FR2882561B1 (fr) | 2005-02-28 | 2007-09-07 | Oreal | Composition anhydre sous forme de film comprenant un polymere filmogene et un colorant direct, preparation et procede de coloration la mettant en oeuvre |
FR2882559B1 (fr) | 2005-02-28 | 2008-03-21 | Oreal | Composition anhydre sous forme de film comprenant un polymere filmogene et un agent oxydant, preparation et procede de traitement de fibres keratiniques la mettant en oeuvre |
FR2883746B1 (fr) | 2005-03-31 | 2007-05-25 | Oreal | Composition colorante comprenant une cellulose et procede de coloration de fibres keratiniques la mettant en oeuvre |
FR2883734B1 (fr) | 2005-03-31 | 2007-09-07 | Oreal | Composition colorante a teneur diminuee en matieres premieres et procede de coloration de fibres keratiniques la mettant en oeuvre |
FR2883737B1 (fr) | 2005-03-31 | 2009-06-12 | Oreal | Composition colorante comprenant un ester de glyceryle et procede de coloration de fibres keratiniques la mettant en oeuvre |
FR2883736B1 (fr) | 2005-03-31 | 2007-05-25 | Oreal | Composition colorante comprenant un ester d'acide gras et procede de coloration de fibres keratiniques la mettant en oeuvre |
US7651533B2 (en) | 2005-03-31 | 2010-01-26 | Oreal | Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor |
FR2883738B1 (fr) | 2005-03-31 | 2007-05-18 | Oreal | Composition colorante comprenant un polymere associatif non ionique, procede de coloration de fibres keratiniques la mettant en oeuvre |
FR2883735B1 (fr) | 2005-03-31 | 2009-06-12 | Oreal | Composition colorante a teneur diminuee en matieres premieres, procede de coloration de fibres keratiniques la mettant en oeuvre et dispositif |
FR2885045B1 (fr) | 2005-04-29 | 2007-06-08 | Oreal | Emulsion inverse comprenant une solution de peroxyde d'hydrogene et une phase inerte de solubilite dans l'eau inferieure a 1% |
US7497878B2 (en) | 2005-06-30 | 2009-03-03 | L'oreal, S.A. | Azo dyes containing a sulphonamide or amide function for the dyeing of human keratin fibers and method of dyeing and dyeing compositions containing them |
FR2889944B1 (fr) | 2005-08-25 | 2007-11-23 | Oreal | Composition tinctoriale comprenant des composes insolubles, procedes mettant en oeuvre cette composition. |
US7905925B2 (en) | 2005-08-25 | 2011-03-15 | L'oreal S.A. | Dye composition comprising at least one insoluble compound and processes using this composition |
FR2889945B1 (fr) | 2005-08-25 | 2011-07-29 | Oreal | Composition de coloration directe comprenant des composes oxygenes insolubles, procedes mettant en oeuvre cette composition. |
FR2889947B1 (fr) | 2005-08-25 | 2012-03-09 | Oreal | Composition oxydante comprenant des composes insolubles, procedes mettant en oeuvre cette composition |
US7481847B2 (en) | 2006-03-28 | 2009-01-27 | L'oreal S.A. | Dye composition comprising at least one cationic hydrazone direct dye, dyeing process, and multi-compartment devices |
FR2901127B1 (fr) | 2006-05-22 | 2012-08-31 | Oreal | Utilisation d'un hydrotrope cationique pour la coloration de fibres keratiniques, composition le comprenant et procedes de coloration la mettant en oeuvre |
FR2901126B1 (fr) | 2006-05-22 | 2012-08-31 | Oreal | Utilisation d'un hydrotrope anionique pour la coloration de fibres keratiniques, composition le comprenant et procedes de coloration la mettant en oeuvre |
FR2917737B1 (fr) | 2007-06-22 | 2012-06-01 | Oreal | Composition de coloration comprenant un compose de type azomethinique a motif pyrazolinone |
FR2929110B1 (fr) | 2008-03-28 | 2010-04-16 | Oreal | Dispersion aqueuse oxydante pour le traitement des fibres keratiniques comprenant un compose amphiphile non ionique a caractere hydrophobe |
FR2940067B1 (fr) | 2008-12-19 | 2011-02-25 | Oreal | Composition oxydante pour le traitement des fibres keratiniques comprenant un polymere cationique, un amide gras et un agent-oxygene |
FR2940090B1 (fr) | 2008-12-19 | 2011-02-25 | Oreal | Composition oxydante pour le traitement des fibres keratiniques comprenant une huile, un alcool gras et un alcool gras oxyalkylene |
FR2944959B1 (fr) | 2009-04-30 | 2011-04-08 | Oreal | Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a motif pyrazolopyridine |
FR2945041B1 (fr) | 2009-04-30 | 2011-04-08 | Oreal | Composes de type azomethinique a motif pyrazolopyridine cationique pour la coloration des fibres keratiniques |
FR3030246B1 (fr) | 2014-12-19 | 2017-02-10 | Oreal | Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a motif pyrazolopyridine |
FR3030522B1 (fr) | 2014-12-19 | 2017-02-10 | Oreal | Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a deux motifs pyrazolopyridines |
WO2017103260A1 (en) | 2015-12-18 | 2017-06-22 | L'oreal | Oxidizing composition for treating keratin materials, comprising a fatty substance and oxyalkylenated surfactants |
FR3045346B1 (fr) | 2015-12-21 | 2019-08-30 | L'oreal | Composition de coloration comprenant un colorant direct de structure triarylmethane, et une silicone |
FR3045331B1 (fr) | 2015-12-21 | 2019-09-06 | L'oreal | Composition de coloration a ph acide comprenant un colorant direct de structure triarylmethane |
FR3052970B1 (fr) | 2016-06-23 | 2018-06-29 | L'oreal | Procede de traitement des fibres keratiniques mettant en œuvre une composition anhydre comprenant un compose de type azomethinique a deux motifs pyrazolopyridines et une composition aqueuse |
FR3052969B1 (fr) | 2016-06-23 | 2020-02-21 | L'oreal | Utilisation pour la coloration des fibres keratiniques d’un compose de type azomethinique a motif derive de quinoline |
FR3053041A1 (fr) | 2016-06-23 | 2017-12-29 | Oreal | Colorant direct de type azomethinique (dis)symetrique comprenant au moins un motif pyrazolopyridine, procede de coloration des fibres keratiniques a partir de ce colorant |
FR3082119B1 (fr) | 2018-06-06 | 2020-05-15 | L'oreal | Procede de coloration et/ou d’eclaircissement des matieres keratiniques |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0850637A1 (de) * | 1996-12-23 | 1998-07-01 | L'oreal | Zusammensetzung zur Oxidationsfärbung von keratinischen Fasern und Färbeverfahren mit dieser Zusammensetzung |
WO2001066646A1 (en) * | 2000-03-09 | 2001-09-13 | Ciba Specialty Chemicals Holding Inc. | A method of colouring hair using cationic dyes |
-
2002
- 2002-09-10 FR FR0211186A patent/FR2844269B1/fr not_active Expired - Fee Related
-
2003
- 2003-09-10 EP EP03292224A patent/EP1398355A1/de not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0850637A1 (de) * | 1996-12-23 | 1998-07-01 | L'oreal | Zusammensetzung zur Oxidationsfärbung von keratinischen Fasern und Färbeverfahren mit dieser Zusammensetzung |
WO2001066646A1 (en) * | 2000-03-09 | 2001-09-13 | Ciba Specialty Chemicals Holding Inc. | A method of colouring hair using cationic dyes |
Also Published As
Publication number | Publication date |
---|---|
FR2844269A1 (fr) | 2004-03-12 |
FR2844269B1 (fr) | 2004-10-15 |
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